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Living an organised life in the cloud, part 4: Projects

This is part 4 of a series of posts which describe the system I use to completely organise my life and everything in it. Part 1 was an introduction, part 2 described Fixed Blocks (FB’s) and part 3 described Anytime Tasks (AT’s). In this part I describe Projects, the last piece of the system I use to organise my time.

Projects have actually been the hardest thing to systematise, probably because no two are the same, and so I expect this part of my system to change the time as I tweak and adjust it for the current conditions of my life, whatever they might be. That said, what I’ve built works brilliantly for me right now.

First things first. What is a project? I define a project as any “task” I want to do, but one which requires either multiple parallel sub-tasks or complex documentation and record keeping. If it’s only a single task, or a simple series of tasks, then an AT is perfect and anything more is process overkill. Importantly implicit in this definition is that anything in any area of my life can be a project, and a few of my current projects include two web apps in differing states of completion, this blog, my Mandarin studies, projects for my job, my jiu jitsu aspirations and – last but not least – my relationship with Katie and what we will do for Christmas.

While it might seem strange at first, even sacrilegious, to call my relationship with my wife a “project”, one thing I’ve learnt over the last few busy busy years is that if I don’t track it then I won’t do it, system or no, and I do not want to let that flame flicker! What’s more, deliberately attending to it also helps me keep track of all the million and one amazing things we come up with to do, to go visit, to see. This means we’re never short of excitement and novelty, and life is made even more invigorating!

With that in mind, what I need to track for each project also becomes clear. In effect, each project is a mini-me, scheduled into FB’s in my overall calendar and complete with project-specific AT’s, References and Ticklers so that it is easy for me to work out what my next action should be as soon as I start work on the project.

When it comes to digital, cloud-based project management applications there is an enormous range, and there are several strong contenders. Popular options include Trello, Asana, Basecamp and MindJet, and while I use Trello, one of this list or something else entirely would be better in other situations. In particular, Trello’s team member updates and news feeds are rudimentary at best (not relevant to my individual projects), and it’s offline support is non-existent (a more serious issue). That said, Trello is extremely flexible, which makes it perfect for the wide variety of projects I have, it’s so flexible I even use it for my Ticklers, and having a common application in this way is really powerful for me.

How I use Trello also varies from project to project, depending on its complexity. “Cards” are the most granular item in Trello, and each card can have any number of checklists, notes and attachments. Ordered sets of cards make up a list, and an ordered set of lists makes up a board, which is the biggest organisational unit in Trello. The easiest way to understand this ontology is probably just to sign up now and have a play, and you can also check out this example board for the Trello project itself, here. In the same vein, the best way to describe how I use Trello is with some examples.

Since a single card can actually be quite detailed, I keep track of my simplest (or currently quiescent) projects on individual cards, organised into an “Other projects” list which is on the “Projects” board. Right now my “Other projects” list includes things like jiu-jitsu, aspirations to sail the Atlantic and the need for me and Katie to figure out where we want to live. Although these don’t store a lot of detail they are exactly right for offloading them from my mind, so I don’t spend any energy remembering them. Projects which are slightly more complex have a list of their own on this board. By reviewing all of these projects once each week I am always reminded as well, and if any of them gets active or complex I can always expand the single cards into a list and the lists into a board.

In a slightly more complex fashion, I keep track of post ideas for this blog in a pair of lists on a “Qua locus” board, one for concrete post ideas I could research and write immediately, and one for ideas that are interesting but which need to be developed further. I drag cards back and forth between these lists and add notes to individual cards as well. Essentially, this arrangement just helps me record my inspiration as it comes to me, again without having to burden my mind – I’d much rather think about what I’m doing than what to do!

As a final example, there is also FiloThought. FiloThought is a complex web application that requires functional and technical design, graphic design, technical implementation and also careful business model and operational thinking. That said, because right now it is just me working on it in my spare time, I still use only a single Trello board for it.

Originally, I used a vertical set of Trello boards – e.g. graphic design, business model and one for each of the major functional components – but this did not work for me in the same way that it also did not work for AT’s. Using a horizontal, contextual approach to projects is another option, but I found that it obscured the often complex dependency amongst the various bits phase based approach instead. This is like in the Trello board, but I’ve tweaked it slightly to my own tastes. Thus I have an Ideas list, a Backlog, a Next Up list, a Known Issues list, an In Progress list, an In Testing list, a Limited Distribution list (not used currently) and a Live list for each major release.

With this set of lists, feature ideas first appear on the Ideas list, where they are fleshed out. Then, as I complete items on the In Progress list (limited to three cards at a time, and I’m aiming to reduce this to 1, for focus), I move something from the Backlog, Next Up or Known Issues list, where each is usually higher priority than the earlier. If I have completed something but believe it needs more testing then I move it to the In Testing list, and eventually I will also do Limited Distribution of new functionality to just a subset of users for evaluation purposes before making it Live in a general release. To help keep track of vertical classifications, I also use the labels feature on Trello, and I use Google docs to record the technical and functional specification plus other long details that don’t lend themselves to a single card.

Now, this kind of phase-based approach might sound complex. On the one hand, this is true, and it takes real effort to update it sensibly. On the other hand though, the project itself is complex and it’s important to manage that complexity, not ignore it. What’s more, this system has become very straight forward to use and also makes it very easy for me to decide what to work on next, the key feature that is absolutely critical. I’m sure I will further improve this system in the future, and I’ll write about it when I do, but for now it is fit for purpose.

To recap the overall life system so far: I organise my time and decide what my next action is using a combination of FB’s, AT’s and Projects. By making it a habit to think up front and put everything in the system it has become very easy for me to figure out what to do at any given moment. I’m also much less stressed because I know I’ve kept track of everything I need to and have not forgotten anything. Thus, these three components are probably the most important parts of the system. However, the components for Ticklers, References, Inspiration and Finance info are also really important, By keeping track of all my other important information it means I don’t have to, an enormous de-stressor for me. More on those in the final parts of this series, and it would be great to know any comments you have on this and the other parts so far as well!